Synthesis of BC ring-systems of taxol by ring-closing metathesis

Synthesis

Volumn , Issue 6, 2000, Pages 869-882

  Bourgeois, Damien ^a   Mahuteau, Jacqueline ^b   Pancrazi, Ange ^c   Nolan, Steven P ^d   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c 5 Mail Gay Lussac   (France)

^d UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

Cyclization; Cyclooctenes; Metathesis; Molybdenum; Olefin; Ruthenium; Taxol

Indexed keywords

PACLITAXEL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; THERMODYNAMICS;

EID: 0034118528     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6263     Document Type: Article

References (47)

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3. (a) Lavelle, F.; Guéritte-Voegelein, F.; Guénard, D. Bull. Cancer, 1993, 80, 326.
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6. For previous work on Taxol synthesis from our laboratory, see: (a) Muller, B.; Delaloge, F.; den Hartog, M.; Férézou, J.-P.; Pancrazi, A.; Prunet, J.; Lallemand, J.-Y. Tetrahedron Lett. 1996, 37, 3313.
7. (b) Delaloge, F.; Prunet, J.; Pancrazi, A.; Lallemand, J.-Y.; Neuman, A.; Prangé, T. Tetrahedron Lett. 1997, 38, 237.
8. (c) Grimaud, L.; Férézou, J.-P.; Prunet, J.; Lallemand, J.-Y. Tetrahedron 1997, 53, 9253.
9. (d) Muller, B.; Férézou, J.-P.; Lallemand, J.-Y.; Pancrazi, A.; Prunet, J.; Prangé, T. Tetrahedron Lett. 1998, 39, 279.
10. (e) Bourgeois, D.; Lallemand, J.-Y.; Pancrazi, A.; Prunet, J. Synlett 1999, 1555.
11. For recent reviews on RCM, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
12. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371.
13. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. For cyclooctene syntheses by RCM, see:
14. (d) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108.
15. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746.
16. (f) Wenz, M.; Großbach, D.; Beitzel, M.; Blechert, S. Synthesis 1999, 607.
17. (g) Paquette, L.; Méndez-Andino, J. Tetrahedron Lett. 1999, 40, 4301. In Ref. 5f, the cyclooctene is a precursor of an AB ring-system of Taxol.
18. For preliminary results, see: Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. Engl. 2000, 39, 725.
19. Mehta, G.; Acharyulu, P. V. R. Tetrahedron Lett. 1993, 34, 8157.
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21. Bourgeois, D.; Maiti, G.; Pancrazi, A.; Prunet, J. Synlett 2000, 323.
22. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
23. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
24. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
25. (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
26. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375.
27. (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
28. (d) For related catalysts, see: Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787.
29. 1H NMR spectrum of the unpurified product.
30. Edwards, S. D.; Lewis, T.; Taylor, R. J. K. Tetrahedron Lett. 1999, 40, 4267.
31. See experimental section for details.
32. The TES ether was deprotected for purification purposes.
33. In reference 6, we have reported a 20% yield for this reaction. In fact, it was performed the first time on a 2:1 diastereomeric mixture of 18. The yield discrepancy is due to the fact that only one diastereomer cyclizes with [Ru].
34. Proof of stereochemistry was obtained by NOESY experiment.
35. Tanino, K.; Shimizu, T.; Kuwahara, M.; Kuwajima, I. J. Org. Chem. 1998, 63, 2422.
36. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137.
37. Proof of stereochemistry for compound 24 will be given later in this article and structure of compound 25 was determined by X-ray diffraction analysis (see Ref. 6).
38. Proof of stereochemistry for compound β-26 will be given later in this article.
39. Nicolaou, K. C.; Nanternet, P. G.; Ueno, H.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1994, 295.
40. Nicolaou, K. C.; Yang, Z.; Sorensen, E. J.; Nakada, M. J. Chem. Soc., Chem. Commun. 1993, 1024.
41. The stucture of compound trans β-28 was determined by X-ray diffraction analysis, see reference 6.
42. In this case, the reaction was complete in 30 min.
43. Hoveyda, A. H. OMCOS X, Versailles, July 18-22, 1999.
44. Fürstner, A.; Langemann, K. Synthesis 1997, 792.
45. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
46. Deprotection of the carbonate moiety of cis β-30 furnished a compound identical to 25 (Scheme 8).
47. α-29 was prepared independently: it is a side product of the hydrogenation of α-23, see Ref. 9.